A reversible COMT inhibitor
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Labeled Version(s)
10010571Entacapone-d10
Metabolite(s)
28046cis-Entacapone
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Entacapone

Item No. 14153

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
2-cyano-3-(3,4-dihydroxy-5-nitrophenyl)-N,N-diethyl-2E-propenamide
CAS Number
130929-57-6
Synonyms
  • OR-611
Molecular Formula
C14H15N3O5
Formula Weight
305.3
Purity
≥98%
Formulation
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 30 mg/mlDMSO: 30 mg/mlDMSO:PBS(pH7.2) (1:1): 0.5 mg/mlEthanol: 5 mg/ml
λmax
224, 309 nm
SMILES
OC1=C(O)C([N+]([O-])=O)=CC(/C=C(C#N)/C(N(CC)CC)=O)=C1
InChi Code
InChI=1S/C14H15N3O5/c1-3-16(4-2)14(20)10(8-15)5-9-6-11(17(21)22)13(19)12(18)7-9/h5-7,18-19H,3-4H2,1-2H3/b10-5+
InChi Key
JRURYQJSLYLRLN-BJMVGYQFSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    10 mg

    $39

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    25 mg

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    50 mg

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    100 mg

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    Product Description

    Entacapone is a reversible catechol O-methyltransferase (COMT) inhibitor (IC50s = 10, 10, 20, and 160 nM for rat duodenum, brain, erythrocyte, and liver COMT, respectively).1 It is selective for COMT over monoamine oxidase A (MAO-A) and MAO-B and phenolsulphotransferase M (PST-M) and PST-P (IC50s = >50 µM). Entacapone (10 mg/kg), in combination with L-DOPA (Item No. 13248) and carbidopa (Item No. 23783), reduces 3-O-methyldopa (3-OMD) levels in the rat striatum and hypothalamus to 52 and 27%, respectively, of the levels in control animals receiving only L-DOPA and carbidopa.2 In a 6-OHDA rat model of Parkinson's disease, entacapone (10 mg/kg), in combination with L-DOPA and benserazide (Item No. 20298), increases contralateral turning behavior and striatal extracellular dopamine levels.3 Entacapone also inhibits contraction of colon longitudinal muscle explants from a 6-OHDA rat model of Parkinson's disease (EC50 = 200 µM).4 Formulations containing entacapone have been used in the treatment of Parkinson's disease.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Nissinen, E., Lindén, I.B., Schultz, E., et al. Biochemical and pharmacological properties of a peripherally acting catechol-O-methyltransferase inhibitor entacapone. Naunyn Schmiedebergs Arch. Pharmacol. 346(3), 262-266 (1992).

    2. Männistö, P.T., Tuomainen, P., and Tuominen, R.K. Different in vivo properties of three new inhibitors of catechol O-methyltransferase in the rat. Br. J. Pharmacol. 105(3), 569-574 (1992).

    3. Gerlach, M., van den Buuse, M., Blaha, C., et al. Entacapone increases and prolongs the central effects of L-DOPA in the 6-hydroxydopamine-lesioned rat. Naunyn Schmiedebergs Arch. Pharmacol. 370(5), 388-394 (2004).

    4. Li, L.-S., Liu, C.-Z., Xu, J.-D., et al. Effect of entacapone on colon motility and ion transport in a rat model of Parkinson’s disease. World J. Gastroenterol. 21(12), 3509-3518 (2015).